SU923368A3 - Process for producing benzimidazole derivatives or their salts - Google Patents
Process for producing benzimidazole derivatives or their salts Download PDFInfo
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- SU923368A3 SU923368A3 SU782685604A SU2685604A SU923368A3 SU 923368 A3 SU923368 A3 SU 923368A3 SU 782685604 A SU782685604 A SU 782685604A SU 2685604 A SU2685604 A SU 2685604A SU 923368 A3 SU923368 A3 SU 923368A3
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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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Abstract
Description
подвергают взаимодействию с галоидны аминоалкилом формулы X-(CHi)n-Ri (VI) где Rn и п имеют вышеуказанные значени ; X - атом галогена, преимущест венно в присутствии конденсирующего агента, такого как окись или гидроокись щелочного металла, предпочтительно в растворителе 1. Соединени формулы (IV) обладают биологически активными свойствами; стимулируют дыхание и центральную нервную систему. Цель изобретени - получение новых соединений, расшир ющих арсенал средств воздействи на живой орга изм . Эта цель достигаетс тем, что со гласно дпособу получени соединений общей формулы (I), который заключаетс в том, что соединение формулы О где R.Rfj и R имеют указанные значени ,, подвергают взаимодействию с соединением формулы Rj-Y (III) где R2) имеет указанные значени ; У - реакционноспособна этерифицированна в сложный эфир оксигруппа , в присутствии основани , такого как карбонат щелочного металла, в случае необходимости в растворителе таком как триамид гексаметилфосфорной кислоты, и выдел ют целевой продукт , в котором R/1-оксиметил, как та ковой или в виде сложного или простого эфира, а целевой продукт, в котором R -карбоксигруппа, выдел ют в виде кислоты или соли. В качестве основани , такого как карбонат щелочног-о металла, предпоч тительно используют карбонат кали . В качестве соединени формулы (Iis reacted with halides with an aminoalkyl of the formula X- (CHi) n -Ri (VI) where Rn and n are as defined above; X is a halogen atom, preferably in the presence of a condensing agent, such as an alkali metal oxide or hydroxide, preferably in solvent 1. The compounds of formula (IV) have biologically active properties; stimulate respiration and central nervous system. The purpose of the invention is to obtain new compounds that expand the arsenal of means of influencing a living organism. This objective is achieved in that, according to the method for producing compounds of general formula (I), which consists in the fact that the compound of the formula O where R.Rfj and R have the indicated meanings is reacted with the compound of the formula Rj-Y (III) where R2 ) has the indicated meanings; Y is a hydroxy esterified esterified ester, in the presence of a base such as an alkali metal carbonate, if necessary in a solvent such as hexamethylphosphoric triamide, and the desired product is isolated in which R / 1-hydroxymethyl is either ester or ether, and the desired product, in which the R-carboxy group, is isolated as an acid or salt. Potassium carbonate is preferably used as a base such as an alkali-carbonate metal. As a compound of formula (I
где Y - реакционноспособна этерифицированна в сложный эфир оксигрупfia . Предпочтительно используют сложкак соли щелочных илн щелочноземельных металлов, например соли натри , кали , а также соли с аммиаком или 84 ный эфир галогенводородной кислоты и спирта формулы . Соединени формулы (1) можно обычным образом превращать в другие соединени формулы (I). Так, соединение формулы (|), где R. означает оксиметил, можно выделить в виде сложного эфира обычным образом , например путем пр мой этерификации соответствующей карбоновой кислотой в присутствии минеральной кислоты , например хлористоводородной или серной, или путем взаимодействи с реакционноспособным производным, например ангидридом,- таким как ангидрид или хлорангидрид, или со сложным эфиром, таким как низший алкиловый или р-нитрофениловый, 2,4-динитрофениловый эфир карбоновой кислоты, в случае необходимости в присутствии кислого или основного конденсирующего средства, Этерификацию в сложный или прос-. той эфир оксиметильной группы можно осуществл ть следующим образом. Перевод т ее сначала обычным образом , например, при помощи фосфортрибромида или тионилхлорида в гало- . генметильную группу, а затем подвергают взаимодействию с соответствующим алкогол том щелочного металла, например алкогол том натри , или с солью щелочного металла, например натриевой, соответствующей карбоновой кислоты. Соединени формулы (1), где R означает карбоксигруппу, можно выделить в виде соли путем обработки основанием или подход щей солью карбоновой кислоты обычным образом, в присутствии растворител или разбавител . Соли можно, в свою очередь,-перевести в соединени формулы (I), где R -карбоксигруппа, обработкой кислым реагентом, например минеральной кислотой . Соединени формулы (I), включа их соли, можно также получать в виде их гидратов. Сол ми соединений формулы (1) вл ютс , например, соли соединений (I), где R/(-карбокси группа, с основани ми,, в частности фармацевтически применимые нетоксичные соли с основани ми, такие аминами, такими как низшие алкиламины или оксиалкиламины, например триметиламин или ди-, три- (2-оксиэтил) амин. Пример 1.2,3г 5- утирил-6-метилбензимидазол-2-метанола раст вор ют в 25 мл триамйда гексаметилфосфорной кислоты, добавл ют 5 г кар боната кали и 1,7 г йодистого метил и перемешивают в течение 12 ч при ко натной температуре. Затем выливают в лед ную воду и экстрагируют этиловым эфиром уксусной кислоты. Выпарив нием и перекристаллизацией из этилового эфира уксусной кислоты/циклогексана получают 5 бутирил-1,6-диметил-2-оксиметил-бензимидазол , т.пл ,5-U2,5°C. Пример 2. Аналогичным образом , как описано в примере 1, получа ют следующие соединени : этиловый эфир 5-бутирил-1,6-диметил-бензимидазол-2-карбоно8ой кислоты . Т.пл. 106-108°С; этиловый эфир Ббутирил-I-метилбензимидазол-2-карбоновой кислоты, т.пл. llS-ny C;. 5-бензоил-1-мeтил-бeнзимидaзoл-2кapбoнoвa кислота; 5 бутирил-1-метил-6-метокси-бензимидазол-2-карбонова кислота, т.пл. выше (с разложение м); 5-Циклопропилкарбонил-1,6-диметил-бензимидазол-2-карбонова кислота . Т.пл. 98-100°С (с разложением); изопропиловый эфир 5 бутирил-1,6-димeтил-бeнзимидaзoл-2-кapбoнoвoй кислоты, т.пл. 90-91С; Б-ацетил-1-мети л-бензимидазол-2-f-i танол. Т.пл. 17б-177°С; 5-бутирил-1-метил-бензимидазол-2метанол . Т.пл. С; 5-бутирил-1-метил-6-хлор-бензимид азол-2-метанол. Т.пл. .183-18.5°С; 5-валерил-1 ,6-диметил-бензимидазол-2-метанол . Т.пл. 125°С; 5-бутирил-1,6-диметил-бензимидазол-2-карбонова кислота, т.пл. выше (с разложением); натриева соль. Т.пл. 275-280°С; 5-ацетил-1-метил-бензимидазол-2карбонова кислота. Т.пл. выше 135°С 5-бутирил-1-метил-бензимидазол ,-2-карбонова кислота. Т.пл. выше , (с разложением) 5-бутирил-1-метиЛ-6-хлор-бензимид азол-2-карбоиова кислота. Т.пл. 90 ( с разложением); 9 8 5-валерил-1,6-диметил-бензимидазол-2-карбонова кислота. Т.пл. выше 88°С (с разложением); 5-бутирил-1-этил-6-метил-бензимидазол-2-карбонова кислота. Т.пл. вые 80°С (с разложением); 5 ацетил-1-бутил-бензимидазол-2карбонова кислота. Т.пл. выше (с разложением); 5-бутирил-1-бутил-6-метил-бензимидазол-2- метанол. Т.пл. 78-81°С; 5-бутирил-2-этоксиметил-1,6-диметил-бензимидазол . Т.пл. , 5-бензоил-1-метил-бензимидазол-2метанол . Т.пл. 168-172 С; 5-бутирил-1-Метил-6-метокси-6ензимидазол-2-метансл . Т.пл. 179-18 С; 5-бутирил-1,6-диметил-2-ацетоксиметил-бензимидазол . Т.пл. 95,5-96 С; 5-оэнантил-1,6-диметил-бензимидазол-2-метанол . Т.пл. 93-93,5 С; 5-пропионил-1,6-диметил-бензимидазол- .-метанол. Т.пл. 13Э-1 0°С; 5-изобутирил-1,6-ди мети л-бензимидазол-2-метанол . Т.пл. 158-1бОС; 5- (2-метилбутирил)-1,6-диметил-бекзимидазол-2-метанол . Т.пл. 158 С; 5-изовалерил-1,6-диметил-бензимидазол-2-метанол . Т.пл. Ii2-l42 ,5С; 5-бутирил-1,6-диметил-2-(2-диметилами ноэтокси метил) -бензимидазол. Т.пл. 108°С. Пример 3. К раствору 5,0 г 5-бутирил-1,6-диметил-бензимидазол-2-метанола в 100 мл метиленхлорида добавл ют 2,36г ацетилхлорида, перемешивают в течение часа при комнатной температуре и затем добавл ют 5 мл триэтиламина. Перемешивают еще 30 мин, встр хивают с раствором бикарбоната натри и дважды с водой, сушат сульфатом натри и упаривают. Получают 2-ацетоксиметил-5 бутирил-1 ,6-диметил-бензимидазол с т.пл. 95,. п Соединени формулы (I) обнаруживают биологически активные свойства. Так, они обладают антиаллергическим действием, что можно показать, наnf iMep , на крысах в дозах от 0,03, до 10 мг/кг при внутривенном применении и в дозах, от 1 до 100 мг/кг при оральном применении в пассивной кожной анафилактической пробе (РСА-реакци ), котора осуществл етс подобно методу, описанному Goose и Blafr, Immunology (т. 16, с. , 19б9), Причей-получаетс пассивна кожна where Y is reactive esterified into oxy group ester. Preferably, alkaline alkaline earth metal salts are used, for example, sodium, potassium salts, as well as salts with ammonia or 84th ester of hydrohalic acid and an alcohol of the formula. The compounds of formula (1) can be converted in the usual manner to other compounds of formula (I). Thus, a compound of the formula (|), where R. is hydroxymethyl, can be isolated as an ester in the usual manner, for example, by direct esterification with a suitable carboxylic acid in the presence of a mineral acid, for example hydrochloric or sulfuric acid, or by reaction with a reactive derivative, for example , - such as anhydride or acid chloride, or with an ester, such as a lower alkyl or p-nitrophenyl carboxylic acid 2,4-dinitrophenyl ester, if necessary in the presence of acidic sludge basic condensing agent, esterification in ester or pros-. That ether of the hydroxymethyl group can be carried out as follows. Translation of it first in the usual way, for example, with the help of phosphorus tribromide or thionyl chloride in halo. a methyl group, and then reacted with an appropriate alkali metal alcoholate, for example sodium alkoxide, or with an alkali metal salt, for example sodium, of the corresponding carboxylic acid. The compounds of formula (1), where R is a carboxy group, can be isolated as a salt by treating it with a base or with a suitable carboxylic acid salt in the usual manner, in the presence of a solvent or diluent. Salts can, in turn, be converted into compounds of formula (I), where R is a carboxy group, by treatment with an acidic reagent, for example a mineral acid. The compounds of formula (I), including their salts, may also be obtained in the form of their hydrates. Salts of the compounds of formula (1) are, for example, salts of the compounds of (I), where R / (is a carboxy group, with bases, in particular pharmaceutically applicable non-toxic salts with bases, such amines, such as lower alkylamines or oxyalkylamines for example, trimethylamine or di-, tri- (2-hydroxyethyl) amine. Example 1.2.3 g of 5-utilyl-6-methylbenzimidazol-2-methanol is dissolved in 25 ml of triamide hexamethylphosphoric acid, 5 g of potassium carbonate and 1 , 7 g of methyl iodide and stirred for 12 hours at a rotate temperature. Then poured into ice water and ec They are strained with ethyl acetate and evaporation and recrystallization from ethyl acetate / cyclohexane gives 5 butyryl-1,6-dimethyl-2-hydroxymethyl-benzimidazole, mp, 5-U2.5 ° C. Example 2. In a similar way as described in Example 1, the following compounds are obtained: 5-Butyryl-1,6-dimethyl-benzimidazole-2-carbonic acid ethyl ester, mp 106-108 ° C; Butyryl-I-methylbenzimidazole-2 ethyl ester -carboxylic acid, so pl. llS-ny C ;. 5-benzoyl-1-methyl-benzimidazole-2-carboxylic acid; 5 butyryl-1-methyl-6-methoxy-benzimidazole-2-carboxylic acid, m.p. above (with decomposition m); 5-Cyclopropylcarbonyl-1,6-dimethyl-benzimidazole-2-carboxylic acid. M.p. 98-100 ° C (with decomposition); 5-butyryl-1,6-dimethyl-benzimidazol-2-carboxylic acid isopropyl ester, m.p. 90-91C; B-acetyl-1-methi l-benzimidazol-2-f-i thanol. M.p. 17b-177 ° C; 5-butyryl-1-methyl-benzimidazole-2 methanol. M.p. WITH; 5-butyryl-1-methyl-6-chlorobenzimide azol-2-methanol. M.p. 183-18.5 ° C; 5-Valeryl-1, 6-dimethyl-benzimidazole-2-methanol. M.p. 125 ° C; 5-butyryl-1,6-dimethyl-benzimidazole-2-carboxylic acid, so pl. above (with decomposition); sodium salt. M.p. 275-280 ° C; 5-acetyl-1-methyl-benzimidazole-2carboxylic acid. M.p. above 135 ° C, 5-butyryl-1-methyl-benzimidazole, -2-carboxylic acid. M.p. above, (with decomposition) 5-butyryl-1-methyl-6-chloro-benzimide azole-2-carboxylic acid. M.p. 90 (with decomposition); 9 8 5-valeryl-1,6-dimethyl-benzimidazole-2-carboxylic acid. M.p. above 88 ° C (with decomposition); 5-butyryl-1-ethyl-6-methyl-benzimidazole-2-carboxylic acid. M.p. 80 ° C (with decomposition); 5 acetyl-1-butyl-benzimidazole-2carboxylic acid. M.p. above (with decomposition); 5-butyryl-1-butyl-6-methyl-benzimidazole-2-methanol. M.p. 78-81 ° C; 5-butyryl-2-ethoxymethyl-1,6-dimethyl-benzimidazole. M.p. , 5-benzoyl-1-methyl-benzimidazole-2 methanol. M.p. 168-172 ° C; 5-Butyryl-1-Methyl-6-methoxy-6-benzimidazole-2-methane. M.p. 179-18 C; 5-butyryl-1,6-dimethyl-2-acetoxymethyl-benzimidazole. M.p. 95.5-96 ° C; 5-oenantil-1,6-dimethyl-benzimidazol-2-methanol. M.p. 93-93.5 C; 5-propionyl-1,6-dimethyl-benzimidazol-methanol. M.p. 13E-1 0 ° C; 5-isobutyryl-1,6-di methy-l-benzimidazole-2-methanol. M.p. 158-1 ° C; 5- (2-methylbutyryl) -1,6-dimethyl-beximidazole-2-methanol. M.p. 158 С; 5-isovaleryl-1,6-dimethyl-benzimidazol-2-methanol. M.p. II-l42, 5C; 5-butyryl-1,6-dimethyl-2- (2-dimethylamine noethoxy methyl) -benzimidazole. M.p. 108 ° C. Example 3. To a solution of 5.0 g of 5-butyryl-1,6-dimethyl-benzimidazole-2-methanol in 100 ml of methylene chloride was added 2.36 g of acetyl chloride, stirred for one hour at room temperature, and then 5 ml of triethylamine were added. Stir for another 30 minutes, shake with sodium bicarbonate solution and twice with water, dry with sodium sulfate and evaporate. Get 2-acetoxymethyl-5 butyryl-1, 6-dimethyl-benzimidazole with so pl. 95 ,. The compounds of formula (I) exhibit biologically active properties. So, they have antiallergic effect, which can be shown on the iMep on rats in doses from 0.03 to 10 mg / kg for intravenous use and in doses from 1 to 100 mg / kg for oral use in a passive skin anaphylactic test. (PCA-reaction), which is carried out similarly to the method described by Goose and Blafr, Immunology (vol. 16, p. 19b9), by passing the passive skin
9 923368109 92336810
ванна в сложный эфир оксигруппа, ис-Источники информации,bath in ester hydroxy group, is-sources of information,
пользуют сложный эфир галогено-прин тые во внимание при экспертизеuse ester halogen-accepted in the examination during
водородной кислоты и спирта фор-1, Патент Великобритании ИГ 1060558,hydrogen acid and alcohol form-1, UK Patent IG 1060558,
мулы Rj-ОН.кл. С 07 d , 1967.Rj-ON.cl mules From 07 d, 1967.
Claims (3)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
LU75684A LU75684A1 (en) | 1976-08-27 | 1976-08-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
SU923368A3 true SU923368A3 (en) | 1982-04-23 |
Family
ID=19728336
Family Applications (7)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU772513755A SU882410A3 (en) | 1976-08-27 | 1977-08-26 | Method of preparing benzacyl-benzimidazol (2)-derivatives |
SU782627856A SU745365A3 (en) | 1976-08-27 | 1978-06-26 | Method of preparing benzacylbenzimidazole-/2/ derivatives or their salts |
SU782685604A SU923368A3 (en) | 1976-08-27 | 1978-11-16 | Process for producing benzimidazole derivatives or their salts |
SU782685606A SU831074A3 (en) | 1976-08-27 | 1978-11-16 | Method of preparing benzimidazole derivatives |
SU782685605A SU843744A3 (en) | 1976-08-27 | 1978-11-16 | Method of preparing devivatives of benzimidazole or their salts |
SU792707652A SU784766A3 (en) | 1976-08-27 | 1979-01-15 | Method of preparing benzacyl-benzimidazole (2) derivatives |
SU792708672A SU888819A3 (en) | 1976-08-27 | 1979-01-15 | Method of preparing derivatives of 5(or 6)-acylated benzimidazolcarboxylic-2 acids or their salts |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU772513755A SU882410A3 (en) | 1976-08-27 | 1977-08-26 | Method of preparing benzacyl-benzimidazol (2)-derivatives |
SU782627856A SU745365A3 (en) | 1976-08-27 | 1978-06-26 | Method of preparing benzacylbenzimidazole-/2/ derivatives or their salts |
Family Applications After (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU782685606A SU831074A3 (en) | 1976-08-27 | 1978-11-16 | Method of preparing benzimidazole derivatives |
SU782685605A SU843744A3 (en) | 1976-08-27 | 1978-11-16 | Method of preparing devivatives of benzimidazole or their salts |
SU792707652A SU784766A3 (en) | 1976-08-27 | 1979-01-15 | Method of preparing benzacyl-benzimidazole (2) derivatives |
SU792708672A SU888819A3 (en) | 1976-08-27 | 1979-01-15 | Method of preparing derivatives of 5(or 6)-acylated benzimidazolcarboxylic-2 acids or their salts |
Country Status (32)
Country | Link |
---|---|
US (3) | US4141982A (en) |
JP (1) | JPS5328172A (en) |
AR (6) | AR224610A1 (en) |
AT (1) | AT359060B (en) |
AU (1) | AU517209B2 (en) |
BE (1) | BE858157A (en) |
CA (1) | CA1098526A (en) |
CH (8) | CH631973A5 (en) |
DD (1) | DD132735A5 (en) |
DE (1) | DE2737462A1 (en) |
DK (1) | DK381277A (en) |
ES (7) | ES461906A1 (en) |
FI (1) | FI68230C (en) |
FR (1) | FR2362841A1 (en) |
GB (2) | GB1595913A (en) |
GR (1) | GR72908B (en) |
HK (1) | HK93784A (en) |
HU (2) | HU186765B (en) |
IE (1) | IE45665B1 (en) |
IL (1) | IL52820A (en) |
LU (1) | LU75684A1 (en) |
MY (1) | MY8500936A (en) |
NL (1) | NL7709471A (en) |
NO (1) | NO148488C (en) |
NZ (1) | NZ185035A (en) |
OA (1) | OA05753A (en) |
PL (4) | PL110215B1 (en) |
PT (1) | PT66947B (en) |
SE (1) | SE434397B (en) |
SG (1) | SG70784G (en) |
SU (7) | SU882410A3 (en) |
ZA (1) | ZA775182B (en) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4312873A (en) * | 1978-09-29 | 1982-01-26 | Syntex (U.S.A.) Inc. | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
US4322431A (en) * | 1979-02-09 | 1982-03-30 | Ciba-Geigy Corporation | Pharmaceutical preparations containing benzimidazole 2-derivatives |
US4492708A (en) * | 1982-09-27 | 1985-01-08 | Eli Lilly And Company | Antiviral benzimidazoles |
DE3772966D1 (en) * | 1987-02-03 | 1991-10-17 | Grace W R & Co | BIOCIDES. |
JPH04197628A (en) * | 1990-11-28 | 1992-07-17 | Sekisui Chem Co Ltd | Manufacture of wall panel |
US5216003A (en) * | 1992-01-02 | 1993-06-01 | G. D. Searle & Co. | Diacid-containing benzimidazole compounds for treatment of neurotoxic injury |
FR2751649B1 (en) * | 1996-07-26 | 1998-08-28 | Adir | NOVEL DERIVATIVES OF BENZIMIDAZOLE, BENZOXAZOLE AND BENZOTHIAZOLE, PROCESS FOR THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
US9663703B2 (en) | 2014-04-25 | 2017-05-30 | James George Clements | Method and compositions for enhanced oil recovery |
CN109467512B (en) * | 2018-12-18 | 2021-06-08 | 苏州开元民生科技股份有限公司 | Synthetic method of 3, 4-diamino-benzophenone |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB766749A (en) | 1954-01-11 | 1957-01-23 | Aschaffenburger Zellstoffwerke | Benzimidazole cobalamines and process for their preparation and separation |
US3318889A (en) * | 1963-10-14 | 1967-05-09 | S B Penick & Company | 2-benzimidazole carbamates |
DE1923481A1 (en) * | 1969-05-08 | 1970-11-12 | Hoechst Ag | Process for the preparation of amides and esters of 1-hydroxy-benzimidazole-2-carboxylic acid |
NL7013343A (en) * | 1969-09-26 | 1971-03-30 | ||
BE759237A (en) * | 1969-11-21 | 1971-05-01 | Montedison Spa | PROCESS FOR PREPARATION OF AMIDES FROM NITROGENOUS HETEROCYCLIC COMPOUNDS |
BE792402A (en) * | 1971-12-07 | 1973-06-07 | Ciba Geigy | NITROGENIC HETEROCYCLIC COMPOUNDS AND ANTHELMINTH AND ANTIMICROBIAL DRUGS WHICH CONTAIN IT |
US4026936A (en) * | 1975-08-07 | 1977-05-31 | Hoffmann-La Roche Inc. | Anthelmintic pyridine and thiazole substituted benzimidazole carbamates |
-
1976
- 1976-08-27 LU LU75684A patent/LU75684A1/xx unknown
-
1977
- 1977-08-01 HU HU811133A patent/HU186765B/en unknown
- 1977-08-01 HU HU77CI1761A patent/HU180700B/en unknown
- 1977-08-18 US US05/825,630 patent/US4141982A/en not_active Expired - Lifetime
- 1977-08-19 DE DE19772737462 patent/DE2737462A1/en not_active Ceased
- 1977-08-22 PT PT66947A patent/PT66947B/en unknown
- 1977-08-23 DD DD7700200697A patent/DD132735A5/en unknown
- 1977-08-24 OA OA56266A patent/OA05753A/en unknown
- 1977-08-25 CA CA285,456A patent/CA1098526A/en not_active Expired
- 1977-08-25 GB GB35710/77A patent/GB1595913A/en not_active Expired
- 1977-08-25 GB GB17219/80A patent/GB1595914A/en not_active Expired
- 1977-08-25 CH CH1040177A patent/CH631973A5/en not_active IP Right Cessation
- 1977-08-25 FR FR7725938A patent/FR2362841A1/en active Granted
- 1977-08-25 FI FI772521A patent/FI68230C/en not_active IP Right Cessation
- 1977-08-25 PL PL1977211468A patent/PL110215B1/en unknown
- 1977-08-25 IL IL52820A patent/IL52820A/en unknown
- 1977-08-25 PL PL1977200449A patent/PL105527B1/en not_active IP Right Cessation
- 1977-08-25 PL PL1977213906A patent/PL112665B1/en unknown
- 1977-08-25 PL PL1977206452A patent/PL108853B1/en unknown
- 1977-08-26 GR GR54237A patent/GR72908B/el unknown
- 1977-08-26 ZA ZA00775182A patent/ZA775182B/en unknown
- 1977-08-26 DK DK381277A patent/DK381277A/en not_active Application Discontinuation
- 1977-08-26 AT AT620677A patent/AT359060B/en not_active IP Right Cessation
- 1977-08-26 SU SU772513755A patent/SU882410A3/en active
- 1977-08-26 NZ NZ185035A patent/NZ185035A/en unknown
- 1977-08-26 NO NO772962A patent/NO148488C/en unknown
- 1977-08-26 BE BE180470A patent/BE858157A/en not_active IP Right Cessation
- 1977-08-26 AU AU28255/77A patent/AU517209B2/en not_active Expired
- 1977-08-26 IE IE1779/77A patent/IE45665B1/en unknown
- 1977-08-26 SE SE7709615A patent/SE434397B/en not_active IP Right Cessation
- 1977-08-26 ES ES461906A patent/ES461906A1/en not_active Expired
- 1977-08-26 NL NL7709471A patent/NL7709471A/en not_active Application Discontinuation
- 1977-08-27 JP JP10312777A patent/JPS5328172A/en active Granted
- 1977-08-29 AR AR268986A patent/AR224610A1/en active
-
1978
- 1978-06-26 SU SU782627856A patent/SU745365A3/en active
- 1978-07-13 ES ES471686A patent/ES471686A1/en not_active Expired
- 1978-07-13 ES ES471688A patent/ES471688A1/en not_active Expired
- 1978-07-13 ES ES471687A patent/ES471687A1/en not_active Expired
- 1978-07-13 ES ES471689A patent/ES471689A1/en not_active Expired
- 1978-07-13 ES ES471690A patent/ES471690A1/en not_active Expired
- 1978-11-16 SU SU782685604A patent/SU923368A3/en active
- 1978-11-16 SU SU782685606A patent/SU831074A3/en active
- 1978-11-16 SU SU782685605A patent/SU843744A3/en active
- 1978-11-20 US US05/962,426 patent/US4213993A/en not_active Expired - Lifetime
-
1979
- 1979-01-15 SU SU792707652A patent/SU784766A3/en active
- 1979-01-15 SU SU792708672A patent/SU888819A3/en active
- 1979-01-18 AR AR275219A patent/AR222318A1/en active
- 1979-01-18 AR AR275218A patent/AR230990A1/en active
- 1979-01-18 AR AR275221A patent/AR225889A1/en active
- 1979-01-18 AR AR275222A patent/AR227621A1/en active
- 1979-01-18 AR AR275220A patent/AR231536A1/en active
- 1979-04-02 ES ES79479189A patent/ES8106706A1/en not_active Expired
- 1979-12-28 US US06/107,980 patent/US4344957A/en not_active Expired - Lifetime
-
1981
- 1981-09-30 CH CH630581A patent/CH631974A5/en not_active IP Right Cessation
- 1981-10-01 CH CH630481A patent/CH632749A5/en not_active IP Right Cessation
- 1981-10-13 CH CH653881A patent/CH631975A5/en not_active IP Right Cessation
- 1981-10-13 CH CH653681A patent/CH632253A5/en not_active IP Right Cessation
-
1982
- 1982-03-23 CH CH177582A patent/CH634305A5/en not_active IP Right Cessation
- 1982-07-27 CH CH455682A patent/CH637121A5/en not_active IP Right Cessation
- 1982-07-27 CH CH455582A patent/CH637120A5/en not_active IP Right Cessation
-
1984
- 1984-10-05 SG SG707/84A patent/SG70784G/en unknown
- 1984-11-29 HK HK937/84A patent/HK93784A/en unknown
-
1985
- 1985-12-30 MY MY936/85A patent/MY8500936A/en unknown
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